There are a lot of elements to this trade that make sense for all parties. One aspect is that all teams remain under the tax.

CHI trade is to simply unlock POR future 1sts. This way CHI gets tangible trade assets rather than waiting and hoping a late first eventually falls to them

Why POR does this?- There is a lot of talk about moving Ant and RWIII. Moving both in one move increases the return. Cronin wants young upside players on extended contracts (Enter Cam Whitmore). Whitmore is only getting playing time when there are injuries. Cronin also wants trade assets that give him flexibility. Getting 1st rd pick swaps and Vanfleet with a huge contract helps. Vanfleet's contract has a team option next year, so POR could flip him like Jru Holiday, trade him at the draft, trade him at the next deadline, or simply make him a buyout guy/ let him walk and get $40+ mil + Green's $8m off the books. Vanfleet has a contract that could help trades with LAL, MIA, MIL, ATL, SAC, and CHI.

Why does HOU do this?- Vanfleet has been good, but he is not on the same timeline as Green, Sengun, Sheppard, Amen, Smith, and Eason. Swapping Vanfleet for Ant gives them a dynamic offensive guard that is 5 years younger and $15+ mil cheaper. Jalen Green does do a lot of similar things, but Simons can play PG and this gives Sengun more space to operate with always having a combo of Ant, Green, and/or Sheppard. HOU also adds RWIII and Thybulle! HOU has depth at C so if RWIII gets hurt it won't ruin their season, but if he is health, he could help them win a playoff series! Thybulle has had some ups/downs but when he is playing he is ELITE on defense and knocks down open 3s around NBA Avg.

This makes a lot of sense to me, but please let me know what you think. If you don't like it tell me why.